1. Field of the Invention
This invention relates to compounds which are the reaction products of C.sub.12-14 -alkyl N-substituted 1,3-diaminopropanes with glutamic acid and/or its C.sub.1-4 -alkyl esters, their alkoxylation products and their salts; as well as the use of these compounds as antimicrobial agents.
2. Statement of the Related Art
N-substituted 1,3-diaminopropanes of the formula: EQU R.sup.1 --NH--CH.sub.2 --CH.sub.2 --CH.sub.2 --NH.sub.2 (I)
wherein R.sup.1 is a C.sub.12-14 linear alkyl
are generally known, and may be conventionally synthesized by reacting the corresponding alkylamines with acrylonitrile, followed by hydrogenation [see Houben-Weyl, Methoden der organischen Chemie, 4th Ed, G. Thieme Verlag, Stuttgart, F.R. Germany, vol. 11/1, p. 564 (1957) as well as U.S. Pat. No. 3,222,402 and corresponding French Pat. No. 1,351,793]. Specific known compounds include N-n-dodecyl- and N-n-tetradecyl-1,3-diaminopropane.
Glutamic acid is also known, as are its C.sub.1-4 -alkyl 5-esters, such as ethyl, n-propyl, n-butyl, and methyl. Processes for the production of glutamic acid-5-esters are described in: U.S. Pat. No. 3,277,156 (and corresponding German published application No. 12 54 635); British Pat. No. 1,080,218 (and corresponding German published application No. 14 93 991); as well as in U.S. Pat. No. 3,770,807 (and corresponding German published application No. 21 58 562). The L-glutamic acid 5-methyl ester is available in the United States from Aldrich Chemical Co., Milwaukee, Wisc., among others.